imatinib   Click here for help

GtoPdb Ligand ID: 5687

Synonyms: CGP 57148 | Gleevec® | Glivec® | STI571
Approved drug PDB Ligand Immunopharmacology Ligand
imatinib is an approved drug (FDA & EMA (2001))
Compound class: Synthetic organic
Comment: Imatinib is a Type-2 kinase inhibitor. Its main inhibitory activity is against ABL kinase, but it has significant action at secondary targets including platelet-derived growth factor receptor (PDGFR) and stem cell growth factor receptor (KIT).

Coronavirus: imatinib is reported to block Spike protein-induced SARS-CoV and MERS-CoV fusion in vitro [8], potentially by blocking Abl2 at the endosomal membrane and disrupting the actin dynamics that are required for virus-host fusion [2]. It will be informative to determine if this holds true for SARS-CoV-2, and whether re-purposing of imatinib and/or newer Abl kinase inhibitors (dasatinib, bosutinib, ponatinib, nilotinib) could be a viable strategy against COVID-19. This approach would likely to be most effective during the early stage of infection.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: imatinib

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 86.28
Molecular weight 493.26
XLogP 3.04
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
Isomeric SMILES CN1CCN(CC1)Cc1ccc(cc1)C(=O)Nc1ccc(c(c1)Nc1nccc(n1)c1cccnc1)C
InChI InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
InChI Key KTUFNOKKBVMGRW-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA & EMA (2001))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
International Nonproprietary Names Click here for help
INN number INN
8031 imatinib
Synonyms Click here for help
CGP 57148 | Gleevec® | Glivec® | STI571
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9659761
Reactome Reaction Reactome logo R-HSA-9669854, R-HSA-9674430, R-HSA-9674095, R-HSA-9669900, R-HSA-9669859, R-HSA-9674397
Other databases
CAS Registry No. 152459-95-5
ChEBI CHEBI:45783
ChEMBL Ligand CHEMBL941
DrugBank Ligand DB00619
DrugCentral Ligand 1423
GtoPdb PubChem SID 178102314
PubChem CID 5291
RCSB PDB Ligand STI
Search Google for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KTUFNOKKBVMGRW
Search PubMed clinical trials imatinib
Search PubMed titles imatinib
Search PubMed titles/abstracts imatinib
SynPHARM 78741 (in complex with ABL proto-oncogene 1, non-receptor tyrosine kinase)
UniChem Compound Search for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KTUFNOKKBVMGRW-UHFFFAOYSA-N
Wikipedia Imatinib